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50-for-50 interview: Penelope Trunk, entrepreneur

There is probably no one on the web today combining such profoundly useful information with such breathtaking personal honesty as Penelope Trunk. Trunk writes about her work life, her family life, and her sex life with equal precision and frankness, and does it all in compulsively readable prose. It would be easy to dismiss her as one of the monsters of self-absorption the Internet has created, were it not for the outsized awareness, intellect, and thoughtfulness she brings to every topic. And I do mean “every”—I come away from her posts about goat herding or the mating rituals of twentysomethings with as many synapses firing as I do her legendarily brilliant pieces on how to navigate the modern workplace. Which is why her blog has consistently resided in my “must-read” folder since I first found it, some seven years ago: Penelope Trunk makes you want to know what’s going on, how it got that way, and what’s coming next. Add to that a generous spirit and a keen appreciation for beauty, and you pretty much have a working description of my favorite kind of artist.

When did you decide to become a writer?

Before I could write, I dictated stories to my dad. But I never thought I’d get paid to write. That just happened because I wrote so much anyway — I had to get good with that much practice.

Who was your favorite teacher?

The teacher who told me she wouldn’t let me come back to school until I called the police and reported my dad for child abuse. I thought she was really mean at the time, and I was scared to tell the police. Now I think she saved my life.

What do you love to write about?

Myself.

What has writing taught you?

That being myself is okay.

How has writing made you stronger?

It helps me sort out my problems and get good feedback quickly.

If you could go back in time and tell 10-year-old you anything, what would it be?

Do what feels good. You probably have a great sense of what you’re good at and what you should be doing. Trust yourself.

What are your five favorite books, blogs or things to read?

Google stuff that you’re interested in and read blogger who write about that. If you like one blog post by one blogger, then read another post. If you like three posts, email the blogger to say hi, and that you like the post. Maybe you will make a new friend.

Penelope Trunk is co-founder of Brazen Careerist, a career management tool for next-generation professionals and her third startup. She decided to be a full-time writer so she did not have to leave her apartment, and started writing career advice for a new generation of workers just as generation Y was becoming a hot topic. That was lucky for her career. Or she is good at spotting trends. Or both. In any case, today Penelope is the author of a bestselling career advice book and the number one career blog. After three years publishing research about how to figure out where to live, Penelope moved to Madison, WI, where she did not fit in well, but she fell in love with a farmer. Now she lives on a farm in southwest Wisconsin. The closest town is Darlington, which has 2000 people in it. She is acclimating to rural life, a process which probably will include home schooling, if she can get enough guts to do it.